KR20060130781A - 다이페닐 인돌-2-온 화합물 및 암 치료에 있어서의 그의용도 - Google Patents
다이페닐 인돌-2-온 화합물 및 암 치료에 있어서의 그의용도 Download PDFInfo
- Publication number
- KR20060130781A KR20060130781A KR1020067023439A KR20067023439A KR20060130781A KR 20060130781 A KR20060130781 A KR 20060130781A KR 1020067023439 A KR1020067023439 A KR 1020067023439A KR 20067023439 A KR20067023439 A KR 20067023439A KR 20060130781 A KR20060130781 A KR 20060130781A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- optionally substituted
- amino
- phenyl
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 50
- 201000011510 cancer Diseases 0.000 title claims abstract description 32
- 238000011282 treatment Methods 0.000 title claims abstract description 14
- -1 Diphenyl Indol-2-one Compound Chemical class 0.000 title claims description 99
- 150000001875 compounds Chemical class 0.000 claims abstract description 148
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000003814 drug Substances 0.000 claims abstract description 26
- 241000124008 Mammalia Species 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- KLAWNELUVVBFGB-UHFFFAOYSA-N 3,3-diphenyl-1h-indol-2-one Chemical class O=C1NC2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 KLAWNELUVVBFGB-UHFFFAOYSA-N 0.000 claims abstract description 12
- IHTKRPXYIKPMQJ-UHFFFAOYSA-N 6-chloro-3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound C12=CC=C(Cl)C(C)=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 IHTKRPXYIKPMQJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 231
- 150000002367 halogens Chemical class 0.000 claims description 130
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 107
- 229910052736 halogen Inorganic materials 0.000 claims description 102
- 125000001072 heteroaryl group Chemical group 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 83
- 150000002431 hydrogen Chemical class 0.000 claims description 61
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 55
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000003107 substituted aryl group Chemical group 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 26
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 25
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 25
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 25
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 150000001721 carbon Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 21
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- SJDACOMXKWHBOW-UHFFFAOYSA-N oxyphenisatine Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2NC1=O SJDACOMXKWHBOW-UHFFFAOYSA-N 0.000 claims description 13
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 9
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
- ITMXRSOBAONPCC-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-methoxy-1h-indol-2-one Chemical compound C12=CC(OC)=CC=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 ITMXRSOBAONPCC-UHFFFAOYSA-N 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 239000002246 antineoplastic agent Substances 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229940127089 cytotoxic agent Drugs 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- PHPUXYRXPHEJDF-UHFFFAOYSA-N oxyphenisatine acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1(C=2C=CC(OC(C)=O)=CC=2)C2=CC=CC=C2NC1=O PHPUXYRXPHEJDF-UHFFFAOYSA-N 0.000 claims description 4
- WXDKMEZYUVTMBX-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-4,5-dimethyl-1h-indol-2-one Chemical compound C12=C(C)C(C)=CC=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WXDKMEZYUVTMBX-UHFFFAOYSA-N 0.000 claims description 3
- UCLAAIWUUBIHBQ-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5,7-dimethyl-1h-indol-2-one Chemical compound CC1=CC(C)=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UCLAAIWUUBIHBQ-UHFFFAOYSA-N 0.000 claims description 3
- HEBOOCSUMSCDNV-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-5-methyl-1h-indol-2-one Chemical compound C12=CC(C)=CC=C2NC(=O)C1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HEBOOCSUMSCDNV-UHFFFAOYSA-N 0.000 claims description 3
- FABLAHMQSQFDHR-UHFFFAOYSA-N 3,3-bis(4-hydroxyphenyl)-7-methyl-1h-indol-2-one Chemical compound CC1=CC=CC2=C1NC(=O)C2(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 FABLAHMQSQFDHR-UHFFFAOYSA-N 0.000 claims description 3
- LBFPJLRSMPVXNZ-UHFFFAOYSA-N 5-bromo-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(Br)=CC=C2NC1=O LBFPJLRSMPVXNZ-UHFFFAOYSA-N 0.000 claims description 3
- CAGNTOOUEJMVHF-UHFFFAOYSA-N 5-chloro-3,3-bis(4-hydroxyphenyl)-1h-indol-2-one Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC(Cl)=CC=C2NC1=O CAGNTOOUEJMVHF-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- CEJCTKIKBAQENM-UHFFFAOYSA-N [4-[3-(4-acetyloxyphenyl)-5-methyl-2-oxo-1h-indol-3-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1(C=2C=CC(OC(C)=O)=CC=2)C2=CC(C)=CC=C2NC1=O CEJCTKIKBAQENM-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
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DKPA200400576 | 2004-04-08 | ||
DKPA200400576 | 2004-04-08 | ||
DKPA200400693 | 2004-05-01 | ||
DKPA200400693 | 2004-05-01 | ||
DKPA200401153 | 2004-07-27 | ||
DKPA200401153 | 2004-07-27 | ||
DKPA200401216 | 2004-08-11 | ||
DKPA200401216 | 2004-08-11 |
Publications (1)
Publication Number | Publication Date |
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KR20060130781A true KR20060130781A (ko) | 2006-12-19 |
Family
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KR1020067023439A Ceased KR20060130781A (ko) | 2004-04-08 | 2005-04-08 | 다이페닐 인돌-2-온 화합물 및 암 치료에 있어서의 그의용도 |
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Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005080335A1 (en) | 2004-02-13 | 2005-09-01 | President And Fellows Of Harvard College | 3-3-di-substituted-oxindoles as inhibitors of translation initiation |
AR056968A1 (es) * | 2005-04-11 | 2007-11-07 | Xenon Pharmaceuticals Inc | Compuestos espiro-oxindol y composiciones farmacéuticas |
MY145694A (en) * | 2005-04-11 | 2012-03-30 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
AR053713A1 (es) * | 2005-04-20 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos heterociclicos y sus usos como agentes terapeuticos |
CN101421625A (zh) * | 2005-10-18 | 2009-04-29 | 乔治梅森知识产权公司 | mTOR途径治疗诊断学 |
MX2009003875A (es) * | 2006-10-12 | 2009-04-22 | Xenon Pharmaceuticals Inc | Derivados y compuestos relacionados de espiro(furo[3,2-c]piridina- 3,3'-indol)-2' (1'h)ona para el tratamiento de enfermedades mediadas por los canales de sodio, tal como dolor. |
CN101631546A (zh) * | 2006-10-12 | 2010-01-20 | 泽农医药公司 | 螺-吲哚酮化合物作为治疗剂的用途 |
WO2008046046A1 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Tricyclic spiro-oxindole derivatives and their uses as therapeutic agents |
EP2102158A1 (en) * | 2006-12-11 | 2009-09-23 | Topo Target A/S | Prodrugs of diphenyl ox- indol- 2 -one compounds for the treatment of cancers |
EP2139856A1 (en) * | 2007-04-24 | 2010-01-06 | Topotarget A/S | Substituted 3-(4-hydroxyphenyl)-indolin-2-one-compounds |
JP4719317B2 (ja) | 2008-02-26 | 2011-07-06 | 武田薬品工業株式会社 | 縮合複素環誘導体およびその用途 |
US20100048913A1 (en) | 2008-03-14 | 2010-02-25 | Angela Brodie | Novel C-17-Heteroaryl Steroidal CYP17 Inhibitors/Antiandrogens;Synthesis In Vitro Biological Activities, Pharmacokinetics and Antitumor Activity |
JP5647098B2 (ja) | 2008-03-21 | 2014-12-24 | ザ ユニヴァーシティー オヴ シカゴ | オピオイド拮抗薬とmTOR阻害薬を用いた治療 |
JP5554337B2 (ja) * | 2008-10-17 | 2014-07-23 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 治療剤としてのスピロオキシインドール化合物およびそれらの使用 |
EP2350091B1 (en) | 2008-10-17 | 2015-06-03 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
US8110578B2 (en) * | 2008-10-27 | 2012-02-07 | Signal Pharmaceuticals, Llc | Pyrazino[2,3-b]pyrazine mTOR kinase inhibitors for oncology indications and diseases associated with the mTOR/PI3K/Akt pathway |
JP2012516900A (ja) | 2009-02-05 | 2012-07-26 | トーカイ ファーマシューティカルズ,インク. | ステロイド性cyp17阻害剤/抗アンドロゲン剤の新しいプロドラッグ |
WO2010109008A1 (en) | 2009-03-26 | 2010-09-30 | Topotarget A/S | Prodrugs of substituted 3-(4-hydroxyphenyl)-indolin-2-ones |
AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
EP2733145A1 (en) | 2009-10-14 | 2014-05-21 | Xenon Pharmaceuticals Inc. | Synthetic methods for spiro-oxindole compounds |
WO2011047173A2 (en) * | 2009-10-14 | 2011-04-21 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
MX2012004624A (es) | 2009-10-23 | 2012-08-23 | Panacela Labs Inc | Metodos para tratar canceres positivos para el receptor de androgenos. |
CN105726531A (zh) | 2010-02-26 | 2016-07-06 | 泽农医药公司 | 用于局部给药的螺-羟吲哚化合物的药物组合物及其作为治疗剂的用途 |
WO2014113820A1 (en) * | 2013-01-18 | 2014-07-24 | Shapiro David J | Estrogen receptor inhibitors |
EP2968370A4 (en) | 2013-03-14 | 2016-09-21 | Univ Maryland | AGENT FOR ANDROGEN RECEPTOR DOWNWARD CONTROL AND USES THEREOF |
JP2016528252A (ja) | 2013-08-12 | 2016-09-15 | トーカイ ファーマシューティカルズ, インコーポレイテッド | アンドロゲン標的治療を使用する新生物障害の処置のためのバイオマーカー |
CA2935167C (en) | 2014-01-16 | 2022-02-22 | Musc Foundation For Research Development | Targeted nanocarriers for the administration of immunosuppressive agents |
TW201636017A (zh) | 2015-02-05 | 2016-10-16 | 梯瓦製藥國際有限責任公司 | 以螺吲哚酮化合物之局部調配物治療帶狀疱疹後遺神經痛之方法 |
EP4470620A3 (en) * | 2018-02-08 | 2025-02-26 | The United States of America, as represented by the Secretary, Department of Health and Human Services | Oxyphenisatin acetate, oxyphenisatin and bisacodyl for treating triple-negative breast cancer |
MX2021000043A (es) | 2018-07-03 | 2021-03-25 | Univ Illinois | Activadores de la respuesta a proteinas desplegadas. |
EP3912625A1 (en) * | 2020-05-20 | 2021-11-24 | Kaerus Bioscience Limited | Novel maxi-k potassium channel openers for the treatment of fragile x associated disorders |
CN114213396B (zh) * | 2022-01-27 | 2023-03-24 | 深圳市乐土生物医药有限公司 | 一种吲哚-2-酮类化合物及其制备方法与用途 |
CN119019312B (zh) * | 2024-10-24 | 2025-01-28 | 苏州宜联生物医药有限公司 | 一种吲哚-2-酮衍生物、其抗体药物偶联物及其应用 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2258505A1 (de) * | 1971-12-02 | 1973-06-07 | Ciba Geigy Ag | Oxindoldiamine und verfahren zu ihrer herstellung |
ES426436A1 (es) * | 1974-05-18 | 1976-07-01 | Andreu Sa Dr | Procedimiento para la obtencion de derivados de la 3,3-bis (4-hidroxifenil)-2-indolinona. |
JPS5590943A (en) * | 1978-12-28 | 1980-07-10 | Fuji Photo Film Co Ltd | Photosensitive material and image forming method applicable thereto |
DE3510730A1 (de) * | 1985-03-08 | 1986-09-11 | Möve-Werk GmbH & Co KG, 7410 Reutlingen | Verfahren zur herstellung eines baumwollgewebes |
US6800658B2 (en) * | 1997-11-20 | 2004-10-05 | Children's Medical Center Corporation | Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment of prevention of diseases characterized by abnormal cell proliferation |
AU745639C (en) * | 1997-11-20 | 2004-02-12 | Children's Medical Center Corporation | Substituted diphenyl indanone, indane and indole compounds and analogues thereof useful for the treatment or prevention of diseases characterized by abnormal cell proliferation |
US6391907B1 (en) * | 1999-05-04 | 2002-05-21 | American Home Products Corporation | Indoline derivatives |
AU2003230581A1 (en) * | 2002-03-15 | 2003-09-29 | Eli Lilly And Company | Dihydroindol-2-one derivatives as steroid hormone nuclear receptor modulators |
WO2005080335A1 (en) * | 2004-02-13 | 2005-09-01 | President And Fellows Of Harvard College | 3-3-di-substituted-oxindoles as inhibitors of translation initiation |
-
2005
- 2005-04-08 AU AU2005230232A patent/AU2005230232A1/en not_active Abandoned
- 2005-04-08 NZ NZ550222A patent/NZ550222A/en unknown
- 2005-04-08 BR BRPI0509745-2A patent/BRPI0509745A/pt not_active IP Right Cessation
- 2005-04-08 WO PCT/DK2005/000244 patent/WO2005097107A2/en active Application Filing
- 2005-04-08 CA CA002562399A patent/CA2562399A1/en not_active Abandoned
- 2005-04-08 EP EP05715161A patent/EP1734951A2/en not_active Withdrawn
- 2005-04-08 KR KR1020067023439A patent/KR20060130781A/ko not_active Ceased
- 2005-04-08 JP JP2007506660A patent/JP2007532496A/ja active Pending
- 2005-04-08 CN CNA2005800102502A patent/CN1953747A/zh active Pending
- 2005-04-08 US US10/599,121 patent/US20070299102A1/en not_active Abandoned
- 2005-04-08 EA EA200601879A patent/EA013209B1/ru not_active IP Right Cessation
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2006
- 2006-09-11 IL IL178012A patent/IL178012A0/en unknown
- 2006-10-05 CR CR8673A patent/CR8673A/es not_active Application Discontinuation
- 2006-10-10 EC EC2006006913A patent/ECSP066913A/es unknown
- 2006-11-02 NO NO20065034A patent/NO20065034L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
NZ550222A (en) | 2010-09-30 |
IL178012A0 (en) | 2006-12-31 |
JP2007532496A (ja) | 2007-11-15 |
ECSP066913A (es) | 2007-02-28 |
CN1953747A (zh) | 2007-04-25 |
BRPI0509745A (pt) | 2007-09-25 |
WO2005097107A8 (en) | 2006-02-16 |
NO20065034L (no) | 2006-11-02 |
AU2005230232A1 (en) | 2005-10-20 |
EA013209B1 (ru) | 2010-04-30 |
WO2005097107A3 (en) | 2006-03-30 |
CR8673A (es) | 2007-07-19 |
WO2005097107A2 (en) | 2005-10-20 |
US20070299102A1 (en) | 2007-12-27 |
CA2562399A1 (en) | 2005-10-20 |
EA200601879A1 (ru) | 2007-04-27 |
EP1734951A2 (en) | 2006-12-27 |
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